FA Cup 1986/87, First Qualifying Round |
 | |  | Oswestry Town | – | Prescot Cables | | 1:0 * |
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FA Cup 1984/85, Second Qualifying Round |
| | | Radcliffe Borough | – | Oswestry Town | | 0:1 |
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FA Cup 1984/85, First Qualifying Round |
| | | Oswestry Town | – | Chadderton | | 4:0 * |
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FA Cup 1983/84, First Qualifying Round |
| | | Wren Rovers | – | Oswestry Town | | 0:2 |
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FA Cup 1982/83, First Qualifying Round |
| | | Oswestry Town | – | Burscough | | 2:1 |
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FA Cup 1979/80, Second Qualifying Round |
| | | Oswestry Town | – | Nantwich Town | | 2:0 |
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FA Cup 1979/80, First Qualifying Round |
| | | Prestwich Heys | – | Oswestry Town | | 0:1 |
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FA Cup 1979/80, Preliminary Round |
| | | Oswestry Town | – | Radcliffe Borough | | 1:0 |
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FA Cup 1978/79, First Qualifying Round |
| | | Oswestry Town | – | St Helens Town | | 3:2 * |
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FA Cup 1977/78, First Qualifying Round |
| | | Oswestry Town | – | Porthmadog | | 2:0 |
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FA Cup 1975/76, First Qualifying Round |
| | | Oswestry Town | – | New Mills | | 5:3 * |
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FA Cup 1974/75, Fourth Qualifying Round |
| | | Mossley | – | Oswestry Town | | 1:3 |
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FA Cup 1974/75, Third Qualifying Round |
| | | Oswestry Town | – | Rhyl |  | 2:1 |
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FA Cup 1974/75, Second Qualifying Round |
| | | Oswestry Town | – | New Brighton | | 2:1 |
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FA Cup 1974/75, First Qualifying Round |
| | | Oswestry Town | – | Blaenau Ffestiniog | | 1:0 * |
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FA Cup 1972/73, First Qualifying Round |
| | | Blaenau Ffestiniog | – | Oswestry Town | | 1:2 |
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FA Cup 1971/72, Third Qualifying Round |
| | | Oswestry Town | – | South Liverpool | | 2:0 |
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FA Cup 1971/72, Second Qualifying Round |
| | | Oswestry Town | – | Connah's Quay Nomads | | 3:1 |
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FA Cup 1971/72, First Qualifying Round |
| | | Oswestry Town | – | Porthmadog | | 2:1 |
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FA Cup 1970/71, Second Qualifying Round |
| | | Oswestry Town | – | Winsford United | | 1:0 * |
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FA Cup 1970/71, First Qualifying Round |
| | | Oswestry Town | – | Kirkby Town | | 2:0 |
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FA Cup 1967/68, First Qualifying Round |
| | | Marine | – | Oswestry Town | | 2:3 |
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FA Cup 1966/67, First Qualifying Round |
| | | Borough United | – | Oswestry Town | | 2:3 |
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FA Cup 1965/66, Third Qualifying Round |
| | | Oswestry Town | – | Macclesfield Town | | 3:2 |
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FA Cup 1965/66, Second Qualifying Round |
| | | Oswestry Town | – | Northwich Victoria | | 3:1 |
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FA Cup 1965/66, First Qualifying Round |
| | | Oswestry Town | – | Congleton Town | | 6:0 |
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FA Cup 1960/61, First Qualifying Round |
| | | Oswestry Town | – | Bromsgrove Rovers | | 3:2 |
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FA Cup 1960/61, Preliminary Round |
| | | Stourbridge | – | Oswestry Town | | 1:4 |
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FA Cup 1959/60, Fourth Qualifying Round |
| | | Oswestry Town | – | Evesham United | | 4:1 |
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FA Cup 1959/60, Third Qualifying Round |
| | | Oswestry Town | – | Bromsgrove Rovers | | 3:1 |
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FA Cup 1959/60, Second Qualifying Round |
| | | Kidderminster Harriers | – | Oswestry Town | | 0:2 |
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FA Cup 1959/60, First Qualifying Round |
| | | Oswestry Town | – | Wellington Town | | 3:1 * |
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FA Cup 1958/59, Third Qualifying Round |
| | | Wellington Town | – | Oswestry Town | | 2:3 |
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FA Cup 1958/59, Second Qualifying Round |
| | | Oswestry Town | – | Bromsgrove Rovers | | 3:0 |
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FA Cup 1958/59, First Qualifying Round |
| | | Oswestry Town | – | Kidderminster Harriers | | 5:3 |
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FA Cup 1957/58, Fourth Qualifying Round |
| | | Oswestry Town | – | Burton Albion | | 5:1 |
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FA Cup 1957/58, Third Qualifying Round |
| | | Wellington Town | – | Oswestry Town | | 0:1 * |
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FA Cup 1957/58, Second Qualifying Round |
| | | Lye Town | – | Oswestry Town | | 1:4 |
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FA Cup 1957/58, First Qualifying Round |
| | | Oswestry Town | – | Stafford Rangers | | 3:0 |
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FA Cup 1957/58, Preliminary Round |
| | | Tamworth | – | Oswestry Town | | 1:2 |
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FA Cup 1954/55, Preliminary Round |
| | | Redditch | – | Oswestry Town | | 0:1 |
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FA Cup 1951/52, Preliminary Round |
| | | Oswestry Town | – | Dudley Town | | 5:2 |
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FA Cup 1950/51, Second Qualifying Round |
| | | Dudley Town | – | Oswestry Town | | 0:1 |
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FA Cup 1950/51, First Qualifying Round |
| | | Oswestry Town | – | Lye Town | | 2:1 |
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FA Cup 1950/51, Extra Preliminary Round |
| | | Oswestry Town | – | Hednesford Town | | 2:1 |
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FA Cup 1887/88, First Round |
| 22.10.1887 | | Llangollen | – | Oswestry Town | | 0:2 * |
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FA Cup 1886/87, First Round |
| 30.10.1886 | | Bollington | – | Oswestry Town | | 2:8 |
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FA Cup 1885/86, First Round |
| 24.10.1885 | | Bollington | – | Oswestry | | 0:5 |
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FA Cup 1883/84, Second Round |
| 01.12.1883 | | Wrexham Olympic | – | Oswestry | | 3:4 |
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FA Cup 1883/84, First Round |
| 10.11.1883 | | Oswestry | – | Hartford St John's | | 2:0 |
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FA Cup 1950/51, Preliminary Round |
| | | Oswestry Town | – | Shrewsbury Town | | +:- |
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